US20210355324A1 - Silicone emulsion composition - Google Patents
Silicone emulsion composition Download PDFInfo
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- US20210355324A1 US20210355324A1 US17/284,666 US201917284666A US2021355324A1 US 20210355324 A1 US20210355324 A1 US 20210355324A1 US 201917284666 A US201917284666 A US 201917284666A US 2021355324 A1 US2021355324 A1 US 2021355324A1
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- United States
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- water
- silicone emulsion
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 175
- 239000000839 emulsion Substances 0.000 title claims abstract description 120
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 60
- 239000002985 plastic film Substances 0.000 claims abstract description 32
- 229920006255 plastic film Polymers 0.000 claims abstract description 32
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 29
- 230000032798 delamination Effects 0.000 claims abstract description 21
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000000758 substrate Substances 0.000 abstract description 50
- 239000000853 adhesive Substances 0.000 abstract description 16
- 230000001070 adhesive effect Effects 0.000 abstract description 16
- 239000010408 film Substances 0.000 description 67
- -1 and among these Substances 0.000 description 51
- 229910052697 platinum Inorganic materials 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 238000000034 method Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229910020447 SiO2/2 Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000004372 Polyvinyl alcohol Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 229910020388 SiO1/2 Inorganic materials 0.000 description 5
- 0 [2*][Si]([2*])([2*])O[Si]([2*])([2*])O[Si](=O)(O[Si]([2*])([2*])O[Si]([2*])([2*])[2*])([Si]([2*])([2*])[2*])[Si]([2*])(=O)(O[Si]([2*])([2*])O[Si]([2*])([2*])[2*])[Si]([2*])([2*])(=O)[Si]([2*])([2*])([2*])=O Chemical compound [2*][Si]([2*])([2*])O[Si]([2*])([2*])O[Si](=O)(O[Si]([2*])([2*])O[Si]([2*])([2*])[2*])([Si]([2*])([2*])[2*])[Si]([2*])(=O)(O[Si]([2*])([2*])O[Si]([2*])([2*])[2*])[Si]([2*])([2*])(=O)[Si]([2*])([2*])([2*])=O 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003060 catalysis inhibitor Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229920006267 polyester film Polymers 0.000 description 3
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910020487 SiO3/2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 150000003058 platinum compounds Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- XQWMWGDTNWOLCD-UHFFFAOYSA-N 3-(3-diethoxysilylpropyl)-3-methyloxolane-2,5-dione Chemical compound CC1(C(=O)OC(C1)=O)CCC[SiH](OCC)OCC XQWMWGDTNWOLCD-UHFFFAOYSA-N 0.000 description 1
- KBDHEPDQEQHASZ-UHFFFAOYSA-N 3-(3-dimethoxysilylpropyl)-3-methyloxolane-2,5-dione Chemical compound CC1(C(=O)OC(C1)=O)CCC[SiH](OC)OC KBDHEPDQEQHASZ-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
- HFYAEUXHCMTPOL-UHFFFAOYSA-N 3-Methyl-1-penten-3-ol Chemical compound CCC(C)(O)C=C HFYAEUXHCMTPOL-UHFFFAOYSA-N 0.000 description 1
- MQSZOZMNAJHVML-UHFFFAOYSA-N 3-phenylbut-1-yn-1-ol Chemical compound OC#CC(C)C1=CC=CC=C1 MQSZOZMNAJHVML-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- NSJAWXMCLJVBPM-UHFFFAOYSA-N CCCCC1CC(=O)OC1=O Chemical compound CCCCC1CC(=O)OC1=O NSJAWXMCLJVBPM-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N CCCCOCC1CO1 Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- QGBMSFLTRRZTGI-UHFFFAOYSA-N CC[SiH](C)C Chemical compound CC[SiH](C)C QGBMSFLTRRZTGI-UHFFFAOYSA-N 0.000 description 1
- KYDHFJZQDCYLDM-UHFFFAOYSA-N C[SiH](C)C.C[Si](C)(C)O[Si](C)(C)O[SiH]1(C)(O[Si](C)(C)O[Si](C)(C)C)O[Si]1(C)(C)=O Chemical compound C[SiH](C)C.C[Si](C)(C)O[Si](C)(C)O[SiH]1(C)(O[Si](C)(C)O[Si](C)(C)C)O[Si]1(C)(C)=O KYDHFJZQDCYLDM-UHFFFAOYSA-N 0.000 description 1
- QKCNFYFOUBQAPA-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)O[Si](C)(C)C Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)O[Si](C)(C)C QKCNFYFOUBQAPA-UHFFFAOYSA-N 0.000 description 1
- INPLRXHMTJZTEX-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)(=O)[Si](C)(C)C Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)(=O)[Si](C)(C)C INPLRXHMTJZTEX-UHFFFAOYSA-N 0.000 description 1
- HXYNAKFUSARECF-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](O[Si](C)(C)O[Si](C)(C)C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)(=O)[Si](C)(C)C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(O[Si](O[Si](C)(C)O[Si](C)(C)C)(O[Si](C)(C)O[Si](C)(C)C)O[Si](C)(C)(=O)[Si](C)(C)C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 HXYNAKFUSARECF-UHFFFAOYSA-N 0.000 description 1
- VOVKVZJTZNYUKG-UHFFFAOYSA-N C[Si](C)(C)O[Si](C)(C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](O[Si](C)(C)O[Si](C)(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 VOVKVZJTZNYUKG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920006197 POE laurate Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910014307 bSiO Inorganic materials 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
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- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 230000002708 enhancing effect Effects 0.000 description 1
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- 150000002118 epoxides Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 229920006137 organovinylpolysiloxane Polymers 0.000 description 1
- NWLSIXHRLQYIAE-UHFFFAOYSA-N oxiran-2-ylmethoxysilicon Chemical compound [Si]OCC1CO1 NWLSIXHRLQYIAE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000000614 phase inversion technique Methods 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 150000004819 silanols Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 125000005625 siliconate group Chemical group 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C09D5/022—Emulsions, e.g. oil in water
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C09D5/024—Emulsion paints including aerosols characterised by the additives
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/40—Adhesives in the form of films or foils characterised by release liners
- C09J7/401—Adhesives in the form of films or foils characterised by release liners characterised by the release coating composition
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- C09J2483/00—Presence of polysiloxane
- C09J2483/005—Presence of polysiloxane in the release coating
Definitions
- the present invention relates to: an addition reaction-curable silicone emulsion composition with favorable adhesion to a plastic film substrate; and a delamination film using this composition.
- silicone compositions for release paper used on a substrate such as paper and plastic
- solvent based silicones have been widely used in view of release properties and for being usable for a comparatively large variety of substrates.
- solvent free silicones is effective as a method for reducing solvent usage.
- an expensive application apparatus and technique are needed, and changing from a solvent based silicone to a solvent free silicone is generally not a method that can be easily adopted.
- solvent free silicone is not favorable due to an increase in production costs.
- emulsion type silicone This type of silicone has been conventionally used, and the following are known: a silicone obtained by mixing an emulsion composed of an organovinylpolysiloxane, a platinum compound, an emulsifier, and water with an emulsion composed of an organohydrogenpolysiloxane, an emulsifier, and water (Patent Document 1); a silicone produced by emulsion polymerization (Patent Document 2); a silicone obtained by emulsifying an organovinylsiloxane and an organohydrogensiloxane using a certain emulsifier and mixing with an emulsion of a platinum compound (Patent Document 3); or the like.
- silicones can be optionally diluted with water, an expensive application apparatus and technique for thin film application are not necessary as opposed to the solvent free type, and there is an advantage that the silicones can be used like the solvent based type.
- emulsion type silicones have not been widely used because of drawbacks associated with having water as a dispersion medium.
- One drawback is that high temperature cure is necessary due to the high latent heat of the evaporation of water, and poor curability is indicated as compared with the solvent based and solvent free types.
- Another drawback is that emulsion type silicones have poor wettability and poor adhesiveness to substrates due to high surface tension of water.
- Patent Document 4 an organopolysiloxane having alkenyl groups at molecular ends
- Patent Document 5 blending an emulsion of a non-silicone polymer
- Patent Document 6 provides a base polymer with a branched structure containing an RSiO 3/2 unit.
- Patent Document 6 an organopolysiloxane containing a large amount of trifunctional siloxane units and alkenyl groups needs to take up 50 mass % or more as an adhesion exhibiting component, and it has been difficult to achieve a sufficiently light release to adhesives (make it easier to peel) when attempting to raise adhesiveness further.
- Patent Document 7 As a means for improving adhesiveness by using a silane coupling agent, it is possible to use a glycidoxy silane (Patent Document 7), but this is mainly applied for in-line purposes.
- Patent Document 8 a method of improving adhesiveness by using an undercoating layer formed using a coating solution containing a silane coupling agent (Patent Document 8) is reported, but the number of steps becomes increased since extension is performed after forming the undercoating layer.
- Patent Document 9 a method of using a silane having an epoxycyclohexyl group
- Patent Document 10 a method of using an additive which is a reaction product of a liquid polyorganosiloxane containing at least one alkenyl group and at least one silanol group with a hydrolysable silane containing at least one epoxide group
- silane coupling agents are often limited to those containing epoxy groups.
- Patent Document 1 JP S57-53143 B
- Patent Document 2 JP S54-52160 A
- Patent Document 3 JP S63-314275 A
- Patent Document 4 JP H6-57144 A
- Patent Document 5 JP H11-222557 A
- Patent Document 6 JP 3824072 B
- Patent Document 7 JP H7-57862 B
- Patent Document 8 JP 6130230 B
- Patent Document 9 JP 5074682 B
- Patent Document 10 JP 2017-504674 A
- the present invention has been made to solve the above-described problems, and an object thereof is to provide: a silicone emulsion composition that gives a cured film adhering well to plastic film substrates regardless of the type, while having suitable release properties regarding adhesives; and a delamination film made by forming a cured film of the silicone emulsion composition.
- the present invention provides an addition reaction-curable silicone emulsion composition
- the water-soluble silane coupling agent (I) has at least one group selected from among a succinic anhydride group, a quaternary ammonium group, and a ureido group, and
- 1 part by mass or more of the water-soluble silane coupling agent (I) is contained relative to 100 parts by mass of the organopolysiloxane (II).
- the inventive addition reaction-curable silicone emulsion composition can give a cured film that adheres well to plastic film substrates regardless of the type, while having suitable release properties regarding adhesives.
- the water-soluble silane coupling agent (I) is preferably represented by the following general formula (Ia),
- R 1 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms and “n” represents 2 or 3; X represents a monovalent hydrocarbon group having 1 to 4 carbon atoms; and “k” represents an integer of 2 to 20.
- Such an addition reaction-curable silicone emulsion composition allows further improvement of adhesiveness to plastic film substrates.
- inventive addition reaction-curable silicone emulsion composition preferably contains the following (1) to (6):
- each R 2 is the same or different, and represents a group selected from an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms and no aliphatic unsaturated bond and an alkenyl group having 2 to 12 carbon atoms optionally having an intervening oxygen atom, and at least two of the R 2 represent alkenyl groups; and “p”, “q”, r1, r2, “s”, and “t” satisfy 10 ⁇ p ⁇ 30,000, 0 ⁇ q, r1, r2 ⁇ 500, and 0 ⁇ s+t 20,
- Such an addition reaction-curable silicone emulsion composition can give a cured film that adheres more favorably to plastic film substrates, and that has excellent release properties regarding adhesives.
- the present invention provides a delamination film having a cured film of the above-described addition reaction-curable silicone emulsion composition formed on a plastic film.
- Such a delamination film has a cured film that adheres well to plastic film substrates while having suitable release properties regarding adhesives, and therefore, has high practicality.
- the inventive addition reaction-curable silicone emulsion composition can be cured to obtain a cured film that can be adhered well to a plastic film substrate regardless of the type of the film substrate. Furthermore, this cured film can be used for a delamination film since the cured film has suitable release properties regarding adhesives. Furthermore, a delamination film obtained by applying the above-described silicone emulsion composition to a plastic film and curing has a cured film formed that adheres well to plastic film substrates while having suitable release properties regarding adhesives, and therefore, has high practicality.
- a silicone emulsion composition obtained by adding a water-soluble silane coupling agent to an alkenyl group-containing organopolysiloxane adheres well to plastic film substrates, and came to complete the present invention.
- the present invention is an addition reaction-curable silicone emulsion composition
- the water-soluble silane coupling agent (I) has at least one group selected from among a succinic anhydride group, a quaternary ammonium group, and a ureido group, and
- 1 part by mass or more of the water-soluble silane coupling agent (I) is contained relative to 100 parts by mass of the organopolysiloxane (II).
- the inventive silicone emulsion composition is cured by addition reaction (addition reaction-curable), contains a water-soluble silane coupling agent (I) and an organopolysiloxane (II) having at least two alkenyl groups in one molecule thereof, where the water-soluble silane coupling agent (I) has at least one group selected from among a succinic anhydride group, a quaternary ammonium group, and a ureido group, and 1 part by mass or more of the water-soluble silane coupling agent (I) is contained relative to 100 parts by mass of the organopolysiloxane (II).
- the inventive addition reaction-curable silicone emulsion composition contains the above-described water-soluble silane coupling agent (I), and therefore, favorable adhesiveness can be achieved even with a plastic film substrate with which sufficient adhesiveness cannot be achieved by addition of a conventionally-used epoxy group-containing silane coupling agent.
- a cured film obtained by curing the inventive composition can maintain sufficient adhesiveness to plastic substrates, while achieving a sufficiently light release to adhesives (making it easier to peel).
- the inventive addition reaction-curable silicone emulsion composition can contain an organohydrogenpolysiloxane (III) having at least two hydrogen atoms each directly bonded to a Si atom in one molecule thereof, a surfactant (IV), a catalytic amount of a platinum group metal-based catalyst (V), and water (VI).
- organohydrogenpolysiloxane (III) having at least two hydrogen atoms each directly bonded to a Si atom in one molecule thereof
- a surfactant (IV) a catalytic amount of a platinum group metal-based catalyst (V)
- V platinum group metal-based catalyst
- the water-soluble silane coupling agent (I) of the present invention is not particularly limited as long as at least one group selected from among a succinic anhydride group, a quaternary ammonium group, and a ureido group is contained.
- the water-soluble silane coupling agent (I) can also contain a hydroxy group, a carboxylic acid group, an amino group, or the like as a group other than the above-described groups. Examples include groups represented by the following general formula.
- “B” represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms
- “m” represents 2 or 3.
- “A” represents a substituted or unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms.
- “1” represents an integer of 2 to 20.
- “Z” represents a succinic anhydride group, a quaternary ammonium group, or a ureido group.
- the water-soluble silane coupling agent (I) can have a hydrolyzed structure or a condensed structure.
- examples include a co-hydrolysis product of a glycidoxyalkyltrialkoxysilane and a tetraalkylammonium salt substituted with a trialkoxysilane, and a co-hydrolysis product of an aminoalkyltrialkoxysilane and a ureidoalkyltrialkoxysilane.
- the water-soluble silane coupling agent (I) is preferably represented by the following general formula
- R 1 represents a monovalent hydrocarbon group having 1 to 10, preferably 1 to 6 carbon atoms.
- alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, and an octyl group
- cycloalkyl groups such as a cyclohexyl group
- alkenyl groups such as a vinyl group, an allyl group, and a propenyl group
- aryl groups such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group
- aralkyl groups such as a benzyl group, a phenylethyl group, and a phenyl
- n represents 2 or 3.
- the silane coupling agent where “n” represents 2 or 3 is preferable since the number of silanols generated by hydrolysis becomes sufficient so that the silane coupling agent has high solubility in water, sufficient stability of the aqueous solution, and high reaction efficiency with inorganic materials.
- X represents a monovalent hydrocarbon group having 1 to 4 carbon atoms, and specific examples include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a tert-butyl group.
- alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and a tert-butyl group.
- a methyl group and an ethyl group are preferable.
- silane coupling agent containing a succinic anhydride group examples include, trimethoxysilylpropyl succinic anhydride, triethoxysilylpropyl succinic anhydride, methyldimethoxysilylpropyl succinic anhydride, methyldiethoxysilylpropyl succinic anhydride, and the like, but the examples are not limited to those shown here.
- water-soluble silane coupling agent (Ia) includes those having a hydrolyzed structure and those having a condensed structure.
- the water-soluble silane coupling agent (I) has at least one group selected from among a succinic anhydride group, a quaternary ammonium group, and a ureido group, these groups exhibit affinity to the film surface, and the silyl group side is bonded to a silicone layer, so that adhesiveness is enhanced.
- the succinic anhydride group exhibits a strong affinity to the film surface and an alkoxysilyl group makes a bond with the silicone layer, so that adhesiveness to the film is enhanced.
- the inventive addition reaction-curable silicone emulsion composition contains 1 part by mass or more of the water-soluble silane coupling agent (I) relative to 100 parts by mass of the organopolysiloxane (II). With less than 1 part by mass, a cured film having sufficient adhesiveness to plastic film substrates cannot be obtained.
- the upper limit of the blended amount of the water-soluble silane coupling agent (I) is not particularly limited and can be determined according to the substrate, but is preferably 30 parts by mass or less, and more preferably 20 parts by mass or less.
- the alkenyl group-containing organopolysiloxane being the main component of the inventive silicone emulsion composition, is not particularly limited as long as the organopolysiloxane has at least two alkenyl groups in one molecule thereof, and does not hinder emulsification and stability of the obtained emulsion. Curing does not take place if the alkenyl group is less than two.
- the organopolysiloxane represented by the following general formula (II-1) is preferably employed to impart more desirable properties to a delamination film obtained with the inventive silicone emulsion composition.
- each R 2 is the same or different, and represents a group selected from an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms and no aliphatic unsaturated bond and an alkenyl group having 2 to 12 carbon atoms optionally having an intervening oxygen atom, and at least two of the R 2 represent alkenyl groups.
- the monovalent hydrocarbon group having 1 to 20 carbon atoms and no aliphatic unsaturated bond include: alkyl groups preferably having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, and a butyl group; cycloalkyl groups preferably having 5 to 8 carbon atoms such as a cyclohexyl group; aryl groups preferably having 6 to 10 carbon atoms such as a phenyl group and a tolyl group; aralkyl groups preferably having 7 to 10 carbon atoms such as a benzyl group; and substituted hydrocarbon groups (for example, a hydroxypropyl group, a chloropropyl group, a 3,3,3-trifluoropropyl group, and the like) obtained by substituting some or all of the hydrogen atoms bonded to the carbon atoms of the above hydrocarbon groups with a hydroxy group, an alkoxy group, a polyether group, an
- alkenyl group having 2 to 12 carbon atoms optionally having an intervening oxygen atom a group represented by —(CH 2 ) x —CH ⁇ CH 2 , wherein “x” represents 0 or an integer of 1 to 10, is preferable.
- a group represented by —(CH 2 ) x —CH ⁇ CH 2 wherein “x” represents 0 or an integer of 1 to 10, is preferable.
- Specific examples include a vinyl group, a propenyl group, a butenyl group, a hexenyl group, an octenyl group, and a decenyl group.
- an ether bond may be included in the methylene chain thereof, and the position where the oxygen atom intervenes, i.e. the position of the ether bond, is not particularly limited. Examples include —(CH 2 ) 2 —O—CH 2 —CH ⁇ CH 2 , —(CH 2 ) 3 —O—CH 2 —CH ⁇ CH 2 , and the
- the viscosity of the organopolysiloxane (II-1) is preferably within a range from 10 mPa ⁇ s to 50000 mPa ⁇ s with 30% toluene diluted viscosity in terms of absolute viscosity at 25° C., more preferably within a range from 50 mPa ⁇ s to 30000 mPa ⁇ s with 30% toluene diluted viscosity.
- the absolute viscosity is 10 mPa ⁇ s or higher, storage stability of the silicone emulsion composition becomes high, and when the absolute viscosity is 50000 mPa ⁇ s or lower with 30% toluene diluted viscosity, emulsification becomes easy.
- organopolysiloxane (II-1) satisfies the above-described viscosity range.
- An organopolysiloxane (II-1) where s+t is 20 or less can be obtained without gelation during synthesis.
- the organopolysiloxane (II) of the present invention can be obtained by known methods for producing an organopolysiloxane. For example, co-hydrolyzing a trialkoxymethylsilane and a dialkenyltetramethyldisiloxane or a hexamethyldisiloxane in an alcohol solvent by using an acid catalyst.
- the acid catalyst include sulfuric acid, hydrochloric acid, phosphoric acid, activated clay, iron chloride, boric acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, and the like.
- the target organopolysiloxane can be obtained by, after neutralizing the reaction product, going through the steps of removing the by-product alcohol and washing with water to remove unreacted materials.
- An alkali catalyst can be also employed as the catalyst.
- Alkali catalysts include KOH, CsOH, NaOH, (CH 3 ) 4 NOH, (n-C 4 H 9 ) 4 POH, and metal siliconates of potassium, phosphorous, and the like.
- organopolysiloxane (II) is a component that greatly affects the release force.
- the release properties of a cured film of the silicone emulsion composition can be varied.
- the organopolysiloxane (II) does not need to be of a single composition.
- an organopolysiloxane (II-1) a mixture of a few organopolysiloxanes having different compositions is possible as long as the average of the multiple components fulfill the requirements of the above-described general formula.
- Specific examples of the organopolysiloxane (II) include the following, but are not limited thereto. Note that Me, Vi, and Ph in the following formulae each represent a methyl group, a vinyl group, and a phenyl group.
- the inventive addition reaction-curable silicone emulsion composition can contain an organohydrogenpolysiloxane (III).
- the organohydrogenpolysiloxane (III) has at least two hydrogen atoms directly bonded to a Si atom (SiH groups) in one molecule thereof. This SiH group undergoes addition reaction with alkenyl groups on the organopolysiloxane (II), and functions as a crosslinking agent for forming a cured film.
- Two or more SiH groups are contained in one molecule, and the structure of a siloxane unit having the groups is represented by the following formula.
- R 3 represents an unsubstituted or substituted monovalent hydrocarbon group, and specific examples include: alkyl groups preferably having 1 to 6 carbon atoms such as a methyl group, an ethyl group, a propyl group, and a butyl group; cycloalkyl groups preferably having 5 to 8 carbon atoms such as a cyclohexyl group; halogen-substituted alkyl groups such as a 3,3,3-trifluoropropyl group; aryl groups preferably having 6 to 10 carbon atoms such as a phenyl group and a tolyl group; aralkyl groups preferably having 7 to 10 carbon atoms such as a benzyl group; and a hydroxypropyl group, a cyanoethyl group, a 3-chloropropyl group, a 3,3,3-trifluoropropyl group, or the like obtained by substituting some or all of the hydrogen atoms
- the blended amount of the organohydrogenpolysiloxane (III) is adjusted according to the amount of alkenyl groups contained in the organopolysiloxane (II), and the molar ratio of SiH groups to alkenyl groups (H/Vi ratio) is preferably within the range of 0.40 to 11.0.
- the blended amount of the organohydrogenpolysiloxane (III) can be set within the range of 1 to 30 parts by mass relative to 100 parts by mass of the organopolysiloxane (II).
- the blended amount is 1 part by mass or more, curability is enhanced, and when the blended amount is 30 parts by mass or less, release force does not exceed practical limits.
- a range of 1 to 15 parts by mass is more preferable.
- the inventive addition reaction-curable silicone emulsion composition can contain a surfactant (IV).
- the surfactant (IV) of the present invention include nonionic types such as alkyl ether types including polyoxyethylene lauryl ether, polyoxyethylene styrenated phenyl ether, polyoxyethylene tridecyl ether, and the like; and alkyl ester types including polyoxyethylene oleate, polyoxyethylene laurate, and the like. Polyoxyethylene lauryl ether and polyoxyethylene styrenated phenyl ether are preferable.
- One of these nonionic emulsifiers can be used alone or a combination of two or more thereof can be used. In order to obtain a stable silicone emulsion composition, it is desirable for the nonionic emulsifier alone or a mixture thereof to have HLB of 10 to 15.
- an anionic surfactant or a cationic surfactant can also be used, but it is desirable to use together with a nonionic surfactant from the aspects of stability of the silicone emulsion and wettability to substrates.
- the anionic surfactant include a higher alcohol sulfuric ester salt, an alkyl phenyl ether sulfuric ester salt, an alkylbenzenesulfonate, a higher alcohol phosphoric ester salt, an ethoxylated higher alcohol sulfuric ester salt, an ethoxylated higher alcohol phosphate, and the like.
- the cationic surfactant include an alkyltrimethylammonium chloride, an alkylamine hydrochloride, an alkylamine acetate, an alkylbenzenedimethylammonium chloride, and the like.
- the blended amount of the surfactant is the minimum amount at which sufficient stability of the silicone emulsion and wettability to substrates can be obtained.
- the blended amount is 0.1 to 20 parts by mass relative to 100 parts by mass of the total amount of the organopolysiloxane (II) and the organohydrogenpolysiloxane (III), preferably 0.5 to 15 parts by mass.
- the amount is 0.1 mass or more, emulsification becomes easy, and when the amount is 20 parts by mass or less, the curability of the silicone emulsion is enhanced.
- a water-soluble resin can be used along with the surfactant.
- the water-soluble resin include a polyvinyl alcohol, cellulose derivatives, Carbopol, and the like, and a polyvinyl alcohol is more preferable.
- This water-soluble resin may function as a thickener. It is preferable to select one having a minimal poisoning action to the platinum group metal-based catalyst (V).
- the blended amount is desirable for the blended amount to be the minimum amount at which sufficient stability of the silicone emulsion and sufficient wettability to substrates can be achieved. Specifically, the amount is preferably 1 to 10 parts by mass relative to 100 parts by mass of the total amount of the organopolysiloxane (II) and the organohydrogenpolysiloxane (III).
- the inventive addition reaction-curable silicone emulsion composition can contain a platinum group metal-based catalyst (V).
- the platinum group metal-based catalyst (V) is a catalyst for promoting addition reaction, and a known addition reaction catalyst can be used.
- a platinum group metal-based catalyst include platinum-based, palladium-based, rhodium-based, and ruthenium-based catalysts and the like, and in particular, platinum-based catalysts are preferably used.
- the platinum-based catalyst include chloroplatinic acid, an alcohol solution or aldehyde solution of chloroplatinic acid, and complexes of chloroplatinic acid with olefins or vinylsiloxanes.
- the platinum group metal-based catalyst is added in a catalytic amount, and from the standpoints of obtaining a favorable cured film and economy, the amount is preferably within the range of 1 to 1000 ppm of platinum group metal relative to the total mass of the organopolysiloxane (II) and the organohydrogenpolysiloxane (III).
- the inventive addition reaction-curable silicone emulsion composition can contain water (VI).
- the amount of the water (VI) is adjusted so as provide a viscosity suitable for the application apparatus to be actually used and a desired silicone coating amount on the substrate, and is not particularly limited. However, the amount is preferably 100 to 10000 parts by mass relative to 100 parts by mass of the organopolysiloxane (II). When the amount is 100 parts by weight or more, an O/W-type emulsion can be easily obtained, and when the amount is 10000 parts by mass or less, stability of the emulsion can be maintained.
- Water having an impurity concentration as in tap water may be used sufficiently, and water that does not contain strong acid, strong alkali, a large amount of alcohol, or salts, etc. is preferable since stability of the emulsion can be maintained.
- the inventive addition reaction-curable silicone emulsion composition can contain optional components.
- the optional components include catalysis inhibitors (controllers) for inhibiting the catalytic activity of platinum group metal-based catalysts, selected from organic nitrogen compounds, organic phosphorus compounds, acetylene-based compounds, oxime compounds, organochlorine compounds, and the like.
- Examples include acetylene-based alcohols such as 3-methyl-1-butyne-3-ol, 3,5-dimethyl-1-hexyne-3-ol, 3-methyl-1-pentene-3-ol, phenylbutynol, and the like; acetylene-based compounds such as 3-methyl-3-1-penten-1-yne, 3,5-dimethyl-1-hexyne-3-yne; a reaction product of these acetylene-based compounds and an alkoxysilane, a siloxane, or a hydrogensilane; vinylsiloxanes such as a cyclic tetramethylvinylsiloxane and the like; organic nitrogen compounds such as a benzotriazole and the like; and organic phosphorus compounds, oxime compounds, organochromium compounds, and the like.
- acetylene-based alcohols such as 3-methyl-1-butyne-3-ol, 3,5-dimethyl-1-hexyne
- silicone resins, silica, or organopolysiloxanes having no hydrogen atoms or alkenyl groups attached to silicon atoms in order to control release properties, it is possible to add silicone resins, silica, or organopolysiloxanes having no hydrogen atoms or alkenyl groups attached to silicon atoms; leveling agents such as fluorochemical surfactants; thickeners such as water-soluble polymers, for example methyl cellulose and polyvinyl alcohol; and the like as necessary.
- leveling agents such as fluorochemical surfactants
- thickeners such as water-soluble polymers, for example methyl cellulose and polyvinyl alcohol; and the like as necessary.
- the amounts of the optional components to be added can be set according to necessity.
- compositions can be employed for producing the inventive addition reaction-curable silicone emulsion composition.
- a high-shear agitating apparatus such as a planetary mixer, a combination mixer, or a high-pressure homogenizer, emulsifying the mixture by phase inversion method, and adding the remainder of the water (VI) for dilution.
- a high-shear agitating apparatus such as a planetary mixer, a combination mixer, or a high-pressure homogenizer, emulsifying the mixture by phase inversion method, and adding the remainder of the water (VI) for dilution.
- One of each component can be used or two or more thereof can be used together.
- the water-soluble silane coupling agent (I) can be added by various methods such as a method of adding to an emulsion solution containing the above (II) to (IV); a method of adding to an emulsion solution containing the above (II) to (VI); adding water to obtain an aqueous solution and then adding; self-emulsification prescription; and a method of blending as a starting material when producing an emulsion solution containing the above (II) to (IV).
- platinum group metal-based catalyst (V) it is desirable to form an emulsion of the above (I) to (IV), and then add the platinum group metal-based catalyst (V) immediately before using this emulsion, rather than emulsifying the platinum group metal-based catalyst (V) simultaneously with the other components.
- the platinum group metal-based catalyst is preferably processed into a water dispersible form before being added. For example, a method of mixing with the surfactant (IV) beforehand and a method of forming an emulsion together by the above-described method are effective.
- the silicone emulsion composition thus prepared can be applied to a plastic film and heat cured to obtain a delamination film which is ready for use.
- plastic film examples include polyolefin films such as biaxially oriented polypropylene films, polyethylene films, and ethylene-propylene copolymer films, and polyester films such as polyethylene terephthalate films.
- the thickness of these film substrates is not restricted, but usually, about 5 to 100 ⁇ m can be applicable.
- a gravure coater In order to apply the inventive composition to a substrate, a gravure coater, air knife coater, roll coater, wire bar or the like may be used.
- the coating amount is not particularly restricted, but is often about 0.1 to 2.0 g/m 2 of silicone solids, preferably 0.1 to 1.0 g/m 2 .
- the coated substrate can be heated at 80° C. to 160° C. for about 5 seconds to 3 minutes in a hot air circulation dryer, for example, for forming a cured film of silicone on the substrate, while imparting release properties.
- the film can be cured by irradiation with infrared or ultraviolet radiation, and combination of these techniques can improve curing efficiency.
- the inventive addition reaction-curable silicone emulsion composition allows a cured film that is excellent in curability and that can be adhered well to a plastic film substrate regardless of the type of the film substrate. Further, this cured film can be used for a delamination film since the cured film has suitable release properties regarding adhesives. Furthermore, a delamination film obtained by applying the above-described silicone emulsion composition to a plastic film and curing. The delamination film has a cured film that adheres well to plastic film substrates while having suitable release properties regarding adhesives, and therefore, has high practicality. Moreover, a cured film of silicone can be formed on the substrate by, after applying the inventive composition, heating the coated substrate at 80° C. to 160° C. for about 5 seconds to 3 minutes. Therefore, a delamination film imparted with release properties can be produced easily without using an expensive apparatus, and without going through a complicated process.
- the siloxane composition was applied to a PET film (DIAFOIL 38 ⁇ m, product name, manufactured by Mitsubishi Chemical Corporation) substrate so as to achieve 0.25 g/m 2 , and heated in a hot air dryer at 150° C. for a predetermined time.
- the formed cured film was rubbed several times with the finger, and visually observed and evaluated whether or not it was smeared and rubbed off. Curability has been represented by the time (seconds) required for curing.
- the siloxane composition was applied to each film substrate so as to achieve 0.25 g/m 2 , and heated in a hot air dryer at 150° C. for a predetermined time.
- the formed cured film was rubbed several times with the finger, and visually observed whether or not it was smeared and rubbed off. This has been reported as adhesiveness.
- a silicone emulsion composition was cured at 150° C. for 30 seconds by the same method as the curability test.
- An adhesive tape Tesa 7475 tape, product name, manufactured by Tesa Tape. Inc.
- Tesa Tape. Inc. with a width of 25 mm was attached thereto, and aged at room temperature for one day. Then, the adhesive tape attached to the sample was peeled using a tensile tester at an angle of 180° at a rate of 0.3 m/min. The force (N/2.5 cm) required for peeling was measured.
- a cured film of a silicone emulsion composition was formed in the same manner as with the release force.
- a polyester adhesive tape (Nitto 31B, product name, manufactured by Nitto Denko Co., Ltd.) was attached to the surface of the cured film, placed under a load of 1976 Pa, and heat treated at 70° C. for 20 hours. Thereafter, the tape was removed and attached to a stainless steel plate, and subsequently, the force (N/2.5 cm) required to peel the treated tape from the stainless steel plate was measured. A percentage of this force to the force required to peel an untreated standard tape has been reported as adhesion retentivity.
- a 5-liter combined emulsifier apparatus (K. T. Combi Mix M model, product name, manufactured by PRIMIX Corporation) including an anchor mixer capable of agitation throughout the vessel and a rotatable disk having small tooth-like protrusions arranged alternately in the upward and downward direction along the periphery was charged with: 100 parts by mass of a siloxane (IIa) composed of 1.9 mol % of a dimethylvinylsiloxane unit represented by (CH 3 ) 2 (CH 2 ⁇ CH)SiO 1/2 , 97.5 mol % of a dimethylsiloxane unit represented by (CH 3 ) 2 SiO 2/2 , and 0.6 mol % of a methylsiloxane unit represented by CH 3 SiO 3/2 , and having a viscosity of 252 mPa ⁇ s and a vinyl group content of 0.027 mol/100 g as an organopolysiloxane (II); 3.58 parts by mass of
- the organopolysiloxane (II) 46.45 parts by mass of a siloxane (IIb) composed of 50 mol % of a dimethylvinylsiloxane unit represented by (CH 3 ) 2 (CH 2 ⁇ CH)SiO 1/2 and 50 mol % of a methylsiloxane unit represented by CH 3 SiO 3/2 , and having a viscosity of 30 mPa ⁇ s and a vinyl group content of 0.60 mol/100 g, 15.83 parts by mass of a siloxane (IIc) having vinyl groups on terminals and side chains composed of 0.03 mol % of a dimethylvinylsiloxane unit represented by (CH 3 ) 2 (CH 2 ⁇ CH)SiO 1/2 , 93.2 mol % of a dimethylsiloxane unit represented by (CH 3 ) 2 SiO 2/2 , 1.80 mol %
- the viscosity was measured with an Ostwald viscometer at 25° C.
- the non-volatile content was measured by a non-volatile residue test method after drying by heating at 105° C. for 3 hours on an aluminum petri dish.
- the obtained reaction product had a viscosity of 17.4 mm 2 /s and a non-volatile content of 31 mass %, and corresponds to a water-soluble silane coupling agent containing a quaternary ammonium group and a hydroxy group.
- the obtained reaction product had a viscosity of 15.7 mm 2 /s and a non-volatile content of 29 mass %, and corresponds to a water-soluble silane coupling agent containing a ureido group and an amino group.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 1.0 parts of a water-soluble silane coupling agent (Ib) represented by the following formula manufactured by Shin-Etsu Chemical Co., Ltd. were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 5.0 parts of the silane coupling agent (Ib) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 12.0 parts of silane coupling agent (Ib) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 20.0 parts of the silane coupling agent (Ib) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 5.0 parts of the silane coupling agent (Ic) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 12.0 parts of the silane coupling agent (Ic) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 3.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 5.0 parts of the silane coupling agent (Id) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 4.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) and 12.0 parts of the silane coupling agent (Id) were blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 4.
- the silicone emulsion 1 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) was blended, and thoroughly mixed. The resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 4.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 4.
- the silicone emulsion 2 was diluted with water, the platinum catalyst emulsion 3 (150 ppm of platinum relative to the silicone content) was blended, and thoroughly mixed.
- the resultant was used as a silicone emulsion composition, and curability, adhesiveness, release force, and adhesion retentivity were measured. The results are shown in Table 4.
- Tables 1 and 2 show the compositions of the Examples and Comparative Examples.
- Patent Document 6 that in conventional art, a large amount of organopolysiloxane containing a large amount of trifunctional siloxane units and alkenyl groups is contained as an adhesion exhibiting component, and that it has been difficult to achieve a sufficiently light release to adhesives (make it easier to peel) when attempting to raise adhesiveness further.
- a cured film obtained by curing the inventive addition reaction-curable silicone emulsion composition having silane coupling agents (Ib), (Ic), and (Id) added can maintain sufficient adhesiveness to plastic substrates, while achieving a sufficiently light release to adhesives.
- the inventive addition reaction-curable silicone emulsion composition allows a cured film that is excellent in curability and that can be adhered well to a plastic film substrate regardless of the type of the film substrate. Furthermore, this cured film can be used for a delamination film since the cured film has suitable release properties regarding adhesives. Furthermore, a delamination film obtained by applying the above-described silicone emulsion composition to a plastic film and curing has a cured film formed that adheres well to plastic film substrates while having suitable release properties regarding adhesives, and therefore, has high practicality. Moreover, a cured film of silicone can be formed on the substrate by, after applying the inventive composition, heating the coated substrate under relatively mild conditions. Therefore, a delamination film imparted with release properties can be produced easily without using an expensive apparatus, and without going through a complicated process.
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- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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| JP2018-202983 | 2018-10-29 | ||
| JP2018202983A JP7074642B2 (ja) | 2018-10-29 | 2018-10-29 | シリコーンエマルジョン組成物 |
| PCT/JP2019/033677 WO2020090209A1 (ja) | 2018-10-29 | 2019-08-28 | シリコーンエマルジョン組成物 |
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| US (1) | US20210355324A1 (ko) |
| EP (1) | EP3875542A4 (ko) |
| JP (1) | JP7074642B2 (ko) |
| KR (1) | KR20210082456A (ko) |
| CN (1) | CN112912443A (ko) |
| TW (1) | TWI828754B (ko) |
| WO (1) | WO2020090209A1 (ko) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20230022811A1 (en) * | 2021-06-25 | 2023-01-26 | Shin-Etsu Chemical Co., Ltd. | Aqueous solution composition containing organosilicon compound |
| US20230021428A1 (en) * | 2021-06-25 | 2023-01-26 | Shin-Etsu Chemical Co., Ltd. | Aqueous solution composition containing organosilicon compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP7414642B2 (ja) * | 2020-05-27 | 2024-01-16 | 信越化学工業株式会社 | 剥離シート用光硬化性オルガノポリシロキサン組成物並びに剥離シート |
| CN113943532A (zh) * | 2021-10-26 | 2022-01-18 | 江苏纳恩新材料有限公司 | 一种水性有机硅乳液及其制备方法 |
| WO2023162587A1 (ja) * | 2022-02-25 | 2023-08-31 | 日本電気硝子株式会社 | コーティング剤 |
| CN114479697A (zh) * | 2022-03-04 | 2022-05-13 | 江苏晶华新材料科技有限公司 | 可降解压敏胶带 |
| KR20230140519A (ko) * | 2022-03-22 | 2023-10-06 | 주식회사 엘지화학 | 이형 조성물 |
| JP2024118254A (ja) * | 2023-02-20 | 2024-08-30 | 信越化学工業株式会社 | シリコーンエマルション組成物 |
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- 2019-08-28 WO PCT/JP2019/033677 patent/WO2020090209A1/ja unknown
- 2019-08-28 KR KR1020217012351A patent/KR20210082456A/ko not_active Application Discontinuation
- 2019-08-28 CN CN201980070649.1A patent/CN112912443A/zh active Pending
- 2019-08-28 EP EP19877602.3A patent/EP3875542A4/en active Pending
- 2019-09-16 TW TW108133198A patent/TWI828754B/zh active
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| US20230021428A1 (en) * | 2021-06-25 | 2023-01-26 | Shin-Etsu Chemical Co., Ltd. | Aqueous solution composition containing organosilicon compounds |
| US11691994B2 (en) * | 2021-06-25 | 2023-07-04 | Shin-Etsu Chemical Co., Ltd. | Aqueous solution composition containing organosilicon compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3875542A4 (en) | 2022-09-14 |
| JP7074642B2 (ja) | 2022-05-24 |
| EP3875542A1 (en) | 2021-09-08 |
| TWI828754B (zh) | 2024-01-11 |
| CN112912443A (zh) | 2021-06-04 |
| KR20210082456A (ko) | 2021-07-05 |
| JP2020070311A (ja) | 2020-05-07 |
| TW202028311A (zh) | 2020-08-01 |
| WO2020090209A1 (ja) | 2020-05-07 |
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